Design rules for optimization of photophysical and kinetic properties of azoarene photoswitches

Adrion, Daniel M.; Lopez, Steven A.

doi:10.1039/d3ob01298k

Org. Biomol. Chem.

2023

DOI: 10.1039/d3ob01298k

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Design rules for optimization of photophysical and kinetic properties of azoarene photoswitches

Daniel M. Adrion,

Steven A. Lopez

Abstract: Azoarenes are an important class of molecular photoswitches that often undergo E➝Z isomerization with ultraviolet light and have short Z-isomer lifetimes. Azobenzene has been a widely studied photoswitch for decades...

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Cited by 2 publications

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Reyes,

Karr,

Ramsperger

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J. Am. Chem. Soc.

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Compartmentalizing Donor–Acceptor Stenhouse Adducts for Structure–Property Relationship Analysis

Reyes,

Karr,

Ramsperger

et al. 2024

J. Am. Chem. Soc.

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Structural and Electronic Properties of Novel Azothiophene Dyes: A Multilevel Study Incorporating Explicit Solvation Effects

Vautrin,

Lambert,

Mahdhaoui

et al. 2024

Molecules

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Among azobenzene derivatives, azothiophenes represent a relatively recent family of compounds that exhibit similar characteristics as dyes and photoreactive systems. Their technological applications are extensive thanks to the additional design flexibility conferred by the heteroaromatic ring. In this study, we present a comprehensive investigation of the structural and electronic properties of novel dyes derived from 3-thiophenamine, utilizing a multilevel approach. We thoroughly examined the potential energy surfaces of the E and Z isomers for three molecules, each bearing different substituents on the phenyl ring at the para position relative to the diazo group. This exploration was conducted through quantum chemistry calculations at various levels of theory, employing a continuum solvent model. Subsequently, we incorporated an explicit solvent (a dimethyl sulfoxide–water mixture) to simulate the most stable isomers using classical molecular dynamics, delivering a clear picture of the local solvation structure and intermolecular interactions. Finally, a hybrid quantum mechanics/molecular mechanics (QM/MM) approach was employed to accurately describe the evolution of the solutes’ properties within their environment, accounting for finite temperature effects.

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Design rules for optimization of photophysical and kinetic properties of azoarene photoswitches

Abstract: Azoarenes are an important class of molecular photoswitches that often undergo E➝Z isomerization with ultraviolet light and have short Z-isomer lifetimes. Azobenzene has been a widely studied photoswitch for decades...

Cited by 2 publications

References 46 publications

Compartmentalizing Donor–Acceptor Stenhouse Adducts for Structure–Property Relationship Analysis

Compartmentalizing Donor–Acceptor Stenhouse Adducts for Structure–Property Relationship Analysis

Structural and Electronic Properties of Novel Azothiophene Dyes: A Multilevel Study Incorporating Explicit Solvation Effects

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